Vacation rentals with outdoor seating in Crook County

Guest suite in Prineville

A spacious bedroom is furnished with a wooden sleigh bed topped with neutral linens and a decorative black blanket. Two bedside lamps illuminate the room. A stylish folding screen provides privacy, and large windows offer scenic views of the valley.

4.93 out of 5 average rating, 245 reviews

Artsy Guest House Nestled in the Rimrock

AlyssaRating, 5 stars1 month ago

Great location, very cozy, and had a beautiful view! The kitchen had everything we needed, the 5 gallon water dispenser, Nespresso pods, and bag of granola were much appreciated! Located close to Smith Rock state park, and the Painted Hills aren’t too far away. This was my first Airbnb I’ve stayed at, so maybe this is standard across all Airbnbs I’m not sure, but I was caught off guard with the extra fees. I stayed 3 nights so I was expecting it to cost $333 plus some sort of service fee, but I ended up paying an extra $180! The service fee was $58, taxes were $41, and then an $80 cleaning fee, even though it’s required to clean up after yourself anyway?? Overall I had a good stay, but was disappointed at the extra fees.

4.94 out of 5 average rating, 52 reviews

A private patio features two Adirondack chairs positioned around a stone firepit, which is lit, casting a warm glow. Strings of lights hang overhead, illuminating the area against a backdrop of a twilight sky, with distant mountains visible in the horizon.

Home in Powell Butte

Modern Brasada Ranch 5 Bed Luxury Home w/ Firepit

GloriaRating, 5 stars8 months ago

Our logging company had been on fires for months and we were trying to give them a relaxing and comfy place to take their days off. Kim was such a wonderful and helpful host, I would absolutely recommend Kim and her lovely home to anyone. We hope to stay again in this lovely home under some different circumstances.

The exterior of the home features large windows, allowing natural light to fill the space. A spacious deck extends from the house, surrounded by natural landscaping with scattered shrubs and trees. The surrounding mountains provide a serene backdrop for this tranquil retreat.

4.97 out of 5 average rating, 32 reviews

Bitterroot Butte | Prineville Reservoir

LeotaRating, 5 stars1 week ago

WOW! What a beautiful home in an amazing setting! It was so peaceful, relaxing and had an incredible view. The beds were comfortable, a nice assortment of spices in the kitchen. Lots of movies to watch and games to play. The layout of the home provided enough space for our whole group. The huge windows overlooking the reservoir were perfect! The stars were outstanding! We had such a great experience, I am trying to figure out when we can come back and stay.

4.96 out of 5 average rating, 53 reviews

A spacious outdoor seating area features a large sectional sofa with bright orange cushions, surrounding a modern fire pit. The deck offers views of the natural landscape and golf course, with a gentle sky and greenery surrounding the space.

Cabin in Powell Butte

Brasada Ranch 2 Master BD/2.5B / Views / Hot Tub

TimothyRating, 5 stars7 months ago

We had a great trip with the family. The Cabin was very spacious, our family of 4 had plenty of room and we were all very comfortable. The living/common spaces were perfect for relaxing or playing games after dinner. The view was beautiful and we loved the back patio. The kitchen was well stocked, the cabin had just about everything you would need. The host is very responsive and even checked in on us after the first day to make sure we had everything we needed, that is top-notch!!! This is by far the best cabin we have stayed at while in Brasada! It was far enough away to be extra quiet, but still very easy to get to the pool and facilities. Parking right in front of the cabin made loading and unloading a breeze.

4.94 out of 5 average rating, 140 reviews

A cozy tiny home with wooden exterior is set against a backdrop of lush greenery. A fire pit sits in the foreground, surrounded by open grass. A deck is visible, featuring a grill and seating area that invite outdoor relaxation.

Tiny home in Prineville

Tiny Pine house in the Ochocos at Wine Down Ranch

MarvinRating, 5 stars3 weeks ago

Had trouble getting through the draft from rain/melted snow because the tesla was a but too low, but they allow me to use their utility terrain vehicles (UTVs) to transfer items from car to our tiny home rental, and they allowed me to use for the couple of days I was there. I thought this was very sweet. Thank you Mary and roy.

5 out of 5 average rating, 92 reviews

A hot tub is illuminated by soft string lights against a wooden fence. The water surface shows gentle ripples, indicating bubbling jets, while a relaxing atmosphere is created by the warm glow surrounding the tub.

Cottage in Prineville

~Quail Run Cottage~

GloriaRating, 5 stars1 month ago

Tera's property was very conveniently located to everything we wanted but was also in a very country and peaceful location. The cottage was spotless! She is very responsive and helpful and we had no issues at all. Would definitely recommend staying here! Also not too long of a drive to all the things you'd want to do in Bend (:

Guest suite in Powell Butte

An outdoor seating area is presented, featuring a stone fireplace. The space includes two sets of rattan chairs with orange cushions and a central coffee table, complemented by a backdrop of natural landscape and distant mountainous views.

4.97 out of 5 average rating, 206 reviews

Panoramic Mountain View Oasis

NicoleRating, 5 stars1 week ago

Tia and Steve were very welcoming and their beautiful home matched the description and photos perfectly. The views from inside the apartment and from the terrace behind it were stunning . The bed was extremely comfortable and we enjoyed the hot tub at sunset. The house is within a half hour drive of fabulous hiking trails and coming back to such luxury after a day of walking was the icing on the cake!

5 out of 5 average rating, 46 reviews

Cabin in Powell Butte

Brasada Ranch Cabin | Hot Tub | Walk to Ranch

TuckerRating, 5 stars1 week ago

We loved staying at Hayley's cabin. The location was great as it is one of the closest cabins to the resort's facilities and very close to the main gate; booking through Airbnb and paying separately for the resort fees was smooth and uncomplicated. What made our stay right off the bat was walking in and finding the sweet gifts left for our boys; nothing starts a family trip off better than cute stuffed animal gifts, they loved it (our five-year-old called it "paradise"). Thank you, Hayley!

4.88 out of 5 average rating, 8 reviews

A built-in gas fire pit provides warmth in a spacious outdoor seating area. Surrounding chairs invite relaxation while offering panoramic views of the Cascade Mountains at sunset. Soft garden lighting enhances the serene ambiance of the expansive lawn.

Home in Powell Butte

The Lookout at Brasada Ranch

MaryRating, 5 stars2 months ago

What a beautiful and clean home. The view was amazing! The description of the home and pictures were accurate. The outdoor patio and fire pit were great! The pool, hot tubs and recreation area were an added bonus but we could have easily just stayed and the home and played games around the nice large dining table. Great family get away with many laugh and great memories! Thank you

Vacation rentals for every style

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Cabins

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Stylish accommodations and amenities

Popular amenities for Crook County outdoor seating rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with outdoor seating

A covered patio area features comfortable seating arrangements and colorful umbrellas. The well-maintained garden includes blooming flowers and pathways made of pavers, providing an inviting space for outdoor relaxation and gatherings.

4.97 out of 5 average rating, 38 reviews

The Juniper House | Prineville Retreat

LoriRating, 5 starstoday

We loved our stay in Prineville! The house was perfect for our group, with a beautiful backyard and patio. It is located right next to a park and about a block from 3rd street, where we could shop and walk to two different food cart pods. Christian made everything easy with his great directions and recommendations.

Superhost

The exterior features a modern home with a large deck and sloped landscape. Two Adirondack chairs are positioned on a gravel patio, surrounded by rocks and greenery. The structure showcases wooden accents and a metal roof, set against a clear blue sky.

Home in Powell Butte

5 out of 5 average rating, 3 reviews

Brasada Ranch | Stunning Views | Couple's Getaway

BrookRating, 5 stars2 months ago

Perfect Space for Creativity & Podcast Recording! We couldn’t have asked for a better place to stay! This Airbnb wasn’t just a home—it was an inspiring, well-thought-out space that elevated our entire experience. We used it as a recording studio for our podcast, and it couldn’t have been more perfect. The acoustics were excellent, the layout allowed for a smooth workflow, and the quiet surroundings made it ideal for focused recording sessions. The natural light and stylish decor created a great atmosphere, both for creative energy and for capturing stunning behind-the-scenes content. Beyond that, the hosts were incredibly thoughtful, ensuring we had everything we needed. The space was spotless, comfortable, and felt like a true retreat after long days of recording. If you’re looking for a place that blends functionality with inspiration—whether for work, creativity, or just relaxation—this is the one. We’ll absolutely be back!

Superhost

The exterior of a modernized 1938 home is displayed, featuring a gray facade with white trim. A covered porch extends from the main entrance, surrounded by a gravel driveway and landscaped areas. Large windows allow for natural light, and trees add greenery to the property.

4.72 out of 5 average rating, 46 reviews

Charming Modernized 1938 Ranch Home

JenniferRating, 5 stars4 months ago

Fantastic yard! My dog loved it. And the central location is fantastic.

A red exterior of the house is framed by a landscaped yard, featuring potted plants on a spacious wooden deck. Large glass doors provide insight into the interior, while steps lead from the yard to the deck, allowing for easy access.

4.91 out of 5 average rating, 44 reviews

Lakeside Spacious 3 Bedroom Home with WiFi.

RalphRating, 5 stars7 months ago

This is a nice home to stay in whether a small or larger group. We enjoyed the view from the deck as well as inside. The house is well supplied, clean and tidy. We also enjoyed a few movies from the wide selection offered. We brought our kayaks. The water is low this time of year but we did get them down the hill. We used the public dock to get them back on the trailer. We've been coming up to the Bend area for years and this was our first time on Prineville. We will come again.